Right after my debut memoir Five Men Who Broke My Heart came out, my editor forwarded me a five-hundred page manuscript from a young guy in Texas I’d never met. His cover letter, addressed to me, bragged that he’d enclosed his true-life story about the five women who’d broken his heart—the male version of my memoir—which he forgot to mention he had bought, skimmed through, or even liked. He was sure I’d want to read his project cloning mine and help get it published. I was semi-amazed he thought I’d find this strategy endearing when I was more apt to call my lawyer than my agent.

Having a mentor seems like such a brilliant idea that many people, like Mr. Texas, fall under the illusion it’s an easy process, and assume everyone will jump at the chance to offer career connections and advice for free. Yet it’s actually harder to land a good mentor than a good marriage partner. Luckily having multiple mentors works better than having multiple marriages, and you can approach, court, and juggle several guides simultaneously.

But before you ask anyone for assistance, beware. Feeble attempts to network, charm, and cajole luminaries often lead to humiliating blunders. One young journalism school graduate recently posted a Craigslist ad titled “Seeking Mentor” that read: “I want to meet someone who is a published author because i know that in order to be successful you have to find out what successful do and take action.” (Suggested action: take a proofreading class.) My buddy Rich Prior, a producer at Sirius Radio, recalled the time he was speaking to a campus group and a senior came up to him and said, “Unlike all the others in the audience who left, I stayed for your whole talk.” The kid seemed to want a medal for his endurance, along with a job, and didn’t even realize he’d already turned off Prior completely.

So instead of estranging the superiors you mean to impress, you need to get a clue. Here are some careful, canny, and classy ways to coerce someone older or wiser into promoting you professionally, along with sure fire methods to immediately alienate all V.I.P.’s in your path.

1. ACT ENTITLED – GET DELETED: Despite your certainty that you’re a genius worthy of immediate attention, successful people are very busy doing their own work. That’s how they became successful. So make sure you’re not coming across as arrogant, presumptuous, impatient, self-involved, flippant, insulting, demanding, or delusional. Don’t assume anybody will assist you out of benevolence or awe, or because you’re so incredibly cool and special. Thousands of recent graduates are begging anybody with a job, company, or name in any field for the same favors. Just because you choose someone doesn’t mean they’ll choose you. Unless you’re approaching your Uncle Dave or your mom’s old college roommate, assume you’ll have to earn the ear or energy of higher ups.

I’m not an agent or an editor who can buy or sell books, yet I get a ridiculous amount of requests to read unsolicited manuscripts and proposals. Recent emails began: “I’ve just completed a hundred thousand words of my debut novel, which I’m sure you’ll find talented and worthy of your expertise…” and “Though I’ve never read any of your work…” which both fell under the heading “Letters We Never Finished Reading…”

2. REAL LIFE IS NOT A REALITY SHOW: Donald Trump will probably not invest in your real estate scheme. The chances of Oprah inviting you on her show to push your product are slim. And I’m betting Salman Rushdie won’t read your unpublished one thousand page opus in twenty-four hours and call your publisher with a fawning blurb. Yes, once in a while pursuing a long-shot will pay off. But it’s easier and faster to first focus on admirable individuals already in your world – a kind boss, coworker, successful older relative, neighbor, doctor, or teacher you admire.

I met most of my mentors at school and work, the best places to mine for powerful allies. The only gurus I didn’t meet that way were the best-selling novelist Howard Fast—who was my cousin—and prolific poet and New York Times editor Harvey Shapiro—who was the former professor of a good friend, so I had a personal introduction. Even so it took me seven years to finagle our first face-to-face meeting.

3. BE UNPREPARED AT YOUR OWN PERIL: In one of my NYU journalism classes, all the young women expressed interest in internships, jobs, or clips from the ultra hip Jane magazine. Yet nobody was having luck with the busy editor, Esther Haynes. Before approaching Haynes, my student Pamela first did a little research and found a funny New York magazine feature article Haynes had penned about a jailhouse love triangle involving the club-kid-turned-murderer Michael Alig. By coincidence, Pamela had once had an odd conversation with Alig at a Chelsea bar and was thus able to start her missive to Haynes: “I loved your piece on Michael Alig—who I’ve actually met. Boy, is that guy obsessed with urine!” Pamela was in Haynes’ office the next day and wound up selling her an essay for $1000. Yes, Pamela was lucky, but she wouldn’t have uncovered the perfect factoid to share had she not taken ten minutes to do her homework.

Check libraries, book stores, web sites, and Google to learn more about the person you want to hire or inspire you. If he’s a professor at your university, look up a description of his classes and try to sit in on a lecture. If she’s a published author, read her books, bio, and attend a reading. Most editors also write. So pitching someone without familiarizing yourself with their publication –and their bylines – is just plain lazy.

Contributing to someone’s pet charity could make you memorable. Neelou, a student last term, came to a soup kitchen reading I hosted at Holy Apostles and bought a copy of Food for the Soul. She emailed how much she enjoyed my anthology, then asked my advice on her work. I wound up editing a rewrite of her essay, and giving her the name of an editor to contact, whom she sold it to. I didn’t help her only because she’d come to an event important to me. But by attending, she sure stood out from my 80 current students and earned my interest and gratitude.

4. DON’T DEMAND TOO MUCH TOO SOON: Proposing a weekly column to an editor you’ve never met is like asking a cute stranger, “Will you go out with me every Saturday night for the next three years?”  That kind of overkill, which makes you look too needy and insecure, will make someone run the other way. Instead for your initial attempt, pitch one short piece and if it goes well (like a good date), you’ll surely get another chance. Similarly, inquiring whether a CEO you don’t know will schedule a private meeting could be conceived as intrusive or inane. However, attending a public speech he’s giving and shaking his hand later might elicit a generous instinct. Keep initial requests small and nonthreatening. Wanting a known novelist to edit your manuscript-in-progress and recommend her agent is unrealistic. But buying her book and asking for her signature could be endearing. Once you’ve made a good impression, ask the person about their next event, or if they have a card, blog or web site, which may offer channels for keeping in touch. Build up to asking bigger favors.

5. DON’T BE A STALKER: Sending a fan letter or email is a much better strategy than showing up at someone’s home or office without an appointment. Don’t phone anyone you don’t know directly unless you have a very close contact.  Instead compose a short, sincere note you can send to their office, agent, manager, or network. Briefly express honest appreciation, making sure you spell their name, company, or book title right. Like many authors, I put an e-mail address on my website. Though I’d usually ignore a total stranger’s request for my editor or agent’s name, I answer nice fan letters from anybody who appears sane.

Someone who came to one of my seminars and wanted more advice afterwards feared that flattering me would make her seem like an ass kisser. I told her “Better to be a kisser upper than a self-involved egotist.”

6. CONNECTIONS CONNECT YOU: Don’t mention the person who sent you on line sixty-seven of your letter—since most readers won’t get that far. The first sentence out of my protégé Isabel’s mouth was “Ruth Gruber gave me your name,” which instantly made me think: Darn, I have to help this person. Why? Because the famous journalist Ruth Gruber helped me. When I contacted my cousin Howard Fast, my initial salutation was, “My mother is Mickey Shapiro.” I knew Howard thought my mother was saucy, so that pretty much nailed me a first meeting. Lavishly praising the person you know in common is common sense. Saying anything that can be construed as remotely insulting about the name you just dropped is asinine.

If you don’t have a direct in, try an indirect one. My students start letters to editors who’ve been guest speakers, “Thanks so much for taking the time to speak to our class. You were inspiring.” Or, after checking with me, they write: “My professor Susan Shapiro gave me your name.” (And not “My professor Susan Shapiro suggested I send you my work so you can publish it, give me lots of money, and make me famous.”) If you have no literal link, but the person is from your hometown or you both graduated from the same school, mention that. Or begin with facts and flattery. “As someone who loved your recent L.A. lecture…” isn’t bad. It could win you a smile, handshake, words of encouragement, a business card, or a flier to the next event. There is only one fast way to endear a writer to you than starting with “As someone who bought your book and loved it…” That’s “As someone who brought five copies of your book for my friends…”

7. ENOUGH ABOUT YOU: Don’t ever begin with how great you are. Saying “As a recent honor graduate of Columbia University, who double majored in English and philosophy,” then going on to list all of your impressive accomplishments, will not impress anyone. If the potential helpmate you’re approaching doesn’t know you, they don’t yet care about your grades or resume. On some level you’re pretty much implying, “I want your job. I want your salary. I want to be the next you.” Are you contacting someone running a charity mentorship program or round-the-clock free career service? No? Then have the brains to praise your target’s accomplishments before launching into how important you are or will be.

This continues to be true during the course of your relationship. My former student Jody recently sent me a long email chronicling every freelance gig she’d had and lost in the seven years since she’d taken my class. At the end she asked to meet so I could help with her next move. I wished her well, but said I was too busy with work deadlines and my current classes. It was true. But had she Googled me first, she would have found I’d sold five books since she’d last seen me. Starting her correspondence with “Mazel tov!” may have gotten her further than “help me, hear me, feed me.”

Naked ambition is ugly; myopia and self-involvement will get you nowhere fast. According to the Robert Greene bestseller The 48 Laws of Power, the individual you hope will be your boss, big sister, or pipeline to prosperity is the master you must bow down to. One executive I know says if the first lines of the cover letter contains three “I’s” in a row, the answer is already no.

8. DON’T TRASH YOURSELF: It stuns me how many aspiring writers unconsciously shoot themselves in the foot by beginning a letter to an editor, “Though I’ve been rejected every time I’ve sent out my work…” or “Though I’m sure you’re not looking for a new freelancer without any experience…” Self-deprecating humor can be engaging when it comes from Chris Rock or Ellen, but don’t try it with someone you don’t know. The loser, slacker, nebbish, neurotic role that works in Woody Allen movies, Philip Roth novels, and David Sedaris essays, is rarely endearing in person. Admitting you’ve been a goof off, lazy, depressed, heartbroken, fired from previous jobs, an alcoholic or drug abuser isn’t so compelling either. Be conscious of your fears and your tendency to reveal way too much, or tell off-color jokes, and other methods of self-sabotage.

9. TRY HUMILITY: If you desperately feel the need to share tales of yourself and your many achievements, don’t show off or exaggerate. “I just finished my third experimental science fiction novel written in German and Spanish which my professor E.L. Doctorow thought was brilliant” means little if these tomes remain unpublished. Unless you’re applying to graduate school, “I was Phi Beta Kappa” makes you sound like a young competitive blow hard. Remember, you’re not greeting your father or Aunt Carla who already care. You’re approaching someone you admire who you’ll never get to know if you don’t rein in your self-regard. Understatement is preferable, along with making your motives clear. “As an aspiring editor who just finished NYU journalism school, it would be an honor to meet you if you ever have five minutes” isn’t a terrible way to conclude a call, email or letter. Writing “As a business major who followed your brilliant recent leverage buyout in the papers, I wondered if you ever needed an intern or unpaid assistant” might lead to a response, an interview, or an internship.

10. NO CONTACT SANS CONTACT INFO: If you want a response to your letter, why are you leaving off your phone number and address? Why not attach a self-addressed stamped envelope? Don’t include an email you don’t check often, or write down an office number if you can’t take calls during the day or check messages over weekends. I know someone who sent out a stack of resumes, then left the country with no laptop or plans to check their voice mail or messages for fourteen days. How self-defeating was that? If you want a reaction, make sure you can be reached easily. Put your first and last name, address, phone numbers, e-mail address, and fax number on any letter, card, or cyber-note. Be careful about sharing link to risqué websites, MySpace and Facebook pages, or embarrassing videos or overly provocative photos of yourself. Don’t assume everyone communicates the same way and loves e-mail, instant messaging or faxing, and has a cell phone, or BlackBerry. Some Luddites still prefer regular mail. At the end of my classes, I send back the last assignments to all of my students who put addresses on their papers. The rest are lost, tossed, or deleted.

In About Writing, the prolific author Samuel R. Delany says: “It’s not my job to copy names and return addresses from envelopes onto manuscripts when the writer was too lazy or too thoughtless to do so…When I receive an envelope in the mail…open it, and remove a manuscript with no name on it, I throw it away immediately…Don’t let a copy, hard or electronic, get six inches away from your keyboard, without containing your name and address, snail mail and e-mail. Make this a habit.” Make this mandatory!

11. YOUR MENTOR ISN’T YOUR HOMIE: Would you tell your co-op board or college admission committee you had an abortion? Or once tried Ecstasy, bulimia, or cutting yourself? No? Then use discretion with your mentor too. Even after you meet, click, get aid, or a job from your guru, don’t spill your guts. You may eventually be asked about your personal life. Please remember that you’re not talking to a blood relation, who will think you’re adorable no matter what, or your therapist, who is paid to hear all of your problems. A busy professional could run the other way if you seem too needy, neurotic, or pathetic. If you’re trying to publish your memoir about the roots of your needy, neurotic, pathetic personality, that’s even more reason to keep the craziness on the page. While acting out may get you a referral for a good counselor or psycho-pharmacologist, nobody wants to go to bat for an emotional basket case.

12: ISSUE PROPER INVITATIONS: Once you’ve established contact with a human you hold in high esteem, by all means extend offers that pay them homage. Especially if real payment is involved too. Most of the editors and agents I’ve asked to speak to my classes and seminars said yes. To coerce them, I used connections and flattery, and phrased my questions specifically, as in, “It would be an honor if you’d consider speaking to my journalism class on Monday May 9th from 7 :00 to 8:00 PM and I can offer one hundred dollar stipend.” After the lecture, I ask if I can treat the speaker to drinks or dinner, and send a thank you note. Asking the brilliant New Yorker humorist Ian Frazier to speak to my class led to his inviting me to co-teach his class, which led to Food for the Soul, the miraculous charity anthology we edited together.

13. SHOW UP, SHUT UP, ANTE UP: Paul, a former protégé, called to say he was sorry he missed my recent readings, panels, and book party. Then he asked for my New York Times editor’s name and my take on how to break into the newspaper of record. I said “Sorry I’m on deadline,” (a writer’s best alibi). I was miffed that he couldn’t make it to my six local book events but – a week later –thought I’d come through for him with another big favor. He might have saved the day by simply saying, “I just ordered your book from Amazon.com. Can’t wait to read it.”

You have to remember that the person who has the least power in any relationship has to compromise and come out of himself the most. So if you’re on the side seeking advice, sympathy, connections, or praise, know that your esteemed guide always has the upper hand. You should expect to attend your mentor’s events (preferably with a group of your friends!), travel to their turf, walk in bearing presents (even if it’s just a congratulations card and Korean deli flowers), offer to treat, supply transportation, give more than you get. Most important, ask questions and listen more than you talk. If Paul ever asks me why I no longer make time for him, I’ll spell it out.

14. RETURN THE FAVOR: Older, powerful people need young blood for fans, assistance, and to keep current. I was happy to publicize projects of my mentors. Now many students I helped get internships a decade ago have risen to the ranks of senior editors and every former pupil I’ve asked to speak to my class has come back. My one-time student David Goodwillie invited me to his book party, gave me a signed copy of his memoir Seemed Like a Good Idea at the Time, and thanked me in the acknowledgments though he’d taken my course five years before. Moved by his gratitude, I invited him to participate in a reading I was doing with my mentor – Harvey Shapiro – whom David had met through our class and admired. The whole evening was a lovefest. Mentors – like elephants – have endless memories and there’s no time limit to generosity. Reaching out to those who went out of their way for you – even decades later – could lead to important lifelong links.

15. BE THE MENTOR YOU WANT: No matter your age or background, consider teaching, tutoring, volunteering to aid those in need, or becoming a big brother or sister to kids lacking a strong role model. Don’t forget the cosmic principle of karma involves circular deeds that create your destiny. So whatever you put out there eventually comes back to you. Being a giving, selfless person who does kind deeds for those less fortunate could be exactly what will make the perfect guru turn around and take you on.